US3749715A - Method of preparing 2,3-dihydro-1h-pyrido-(2,3-b)(1,4)-thiazin-2-ones - Google Patents

Method of preparing 2,3-dihydro-1h-pyrido-(2,3-b)(1,4)-thiazin-2-ones Download PDF

Info

Publication number: US3749715A
Authority: US; United States
Prior art keywords: dihydro; pyrido; preparing; thiazin; ones
Prior art date: 1971-01-20
Legal status (The legal status is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the status listed.): Expired - Lifetime

Application number

US00108206A

Other languages

English (en)

Inventor

R Stein

C Nordeen

Current Assignee (The listed assignees may be inaccurate. Google has not performed a legal analysis and makes no representation or warranty as to the accuracy of the list.)

Abbott Laboratories

Original Assignee

Abbott Laboratories

Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)

1971-01-20

Filing date

1971-01-20

Publication date

1973-07-31

1971-01-20 Application filed by Abbott Laboratories filed Critical Abbott Laboratories

1973-07-31 Application granted granted Critical

1973-07-31 Publication of US3749715A publication Critical patent/US3749715A/en

1990-07-31 Anticipated expiration legal-status Critical

Status Expired - Lifetime legal-status Critical Current

Links

238000000034 method Methods 0.000 title abstract description 8
BOASKSPVGGTZKJ-UHFFFAOYSA-N 1h-pyrido[2,3-b][1,4]thiazin-2-one Chemical class C1=CC=C2NC(=O)CSC2=N1 BOASKSPVGGTZKJ-UHFFFAOYSA-N 0.000 title description 2
239000002253 acid Substances 0.000 abstract description 7
LKNPLDRVWHXGKZ-UHFFFAOYSA-N 3-nitro-1h-pyridine-2-thione Chemical compound [O-][N+](=O)C1=CC=CN=C1S LKNPLDRVWHXGKZ-UHFFFAOYSA-N 0.000 abstract description 4
DQOOELMGDDSIBB-UHFFFAOYSA-N 2,3-dihydro-1h-pyrido[2,3-b][1,4]thiazine Chemical compound C1=CC=C2NCCSC2=N1 DQOOELMGDDSIBB-UHFFFAOYSA-N 0.000 abstract description 2
229910052739 hydrogen Inorganic materials 0.000 description 10
239000001257 hydrogen Substances 0.000 description 10
125000002496 methyl group Chemical group [H]C([H])([H])* 0.000 description 10
125000001246 bromo group Chemical group Br* 0.000 description 4
238000006243 chemical reaction Methods 0.000 description 4
150000001875 compounds Chemical class 0.000 description 4
125000004435 hydrogen atom Chemical group [H]* 0.000 description 4
XLYOFNOQVPJJNP-UHFFFAOYSA-N water Substances O XLYOFNOQVPJJNP-UHFFFAOYSA-N 0.000 description 4
HKNNERRQSVWCFL-UHFFFAOYSA-N 3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=C=N[CH]1 HKNNERRQSVWCFL-UHFFFAOYSA-N 0.000 description 3
QTBSBXVTEAMEQO-UHFFFAOYSA-N Acetic acid Chemical compound CC(O)=O QTBSBXVTEAMEQO-UHFFFAOYSA-N 0.000 description 3
WEVYAHXRMPXWCK-UHFFFAOYSA-N Acetonitrile Chemical compound CC#N WEVYAHXRMPXWCK-UHFFFAOYSA-N 0.000 description 3
UFHFLCQGNIYNRP-UHFFFAOYSA-N Hydrogen Chemical compound [H][H] UFHFLCQGNIYNRP-UHFFFAOYSA-N 0.000 description 3
KWYUFKZDYYNOTN-UHFFFAOYSA-M Potassium hydroxide Chemical compound [OH-].[K+] KWYUFKZDYYNOTN-UHFFFAOYSA-M 0.000 description 3
150000002431 hydrogen Chemical group 0.000 description 3
UUOLETYDNTVQDY-UHFFFAOYSA-N 2-chloro-3-nitropyridine Chemical compound [O-][N+](=O)C1=CC=CN=C1Cl UUOLETYDNTVQDY-UHFFFAOYSA-N 0.000 description 2
IAZDPXIOMUYVGZ-UHFFFAOYSA-N Dimethylsulphoxide Chemical compound CS(C)=O IAZDPXIOMUYVGZ-UHFFFAOYSA-N 0.000 description 2
ZHNUHDYFZUAESO-UHFFFAOYSA-N Formamide Chemical compound NC=O ZHNUHDYFZUAESO-UHFFFAOYSA-N 0.000 description 2
125000002915 carbonyl group Chemical group [*:2]C([*:1])=O 0.000 description 2
125000001309 chloro group Chemical group Cl* 0.000 description 2
125000001495 ethyl group Chemical group [H]C([H])([H])C([H])([H])* 0.000 description 2
125000001153 fluoro group Chemical group F* 0.000 description 2
125000002346 iodo group Chemical group I* 0.000 description 2
238000004519 manufacturing process Methods 0.000 description 2
KMBNEGCONOTJPE-UHFFFAOYSA-N 1h-pyrido[2,3-b][1,4]thiazine Chemical class C1=CC=C2NC=CSC2=N1 KMBNEGCONOTJPE-UHFFFAOYSA-N 0.000 description 1
XNWFRZJHXBZDAG-UHFFFAOYSA-N 2-METHOXYETHANOL Chemical compound COCCO XNWFRZJHXBZDAG-UHFFFAOYSA-N 0.000 description 1
125000001494 2-propynyl group Chemical group [H]C#CC([H])([H])* 0.000 description 1
AGIJRRREJXSQJR-UHFFFAOYSA-N 2h-thiazine Chemical compound N1SC=CC=C1 AGIJRRREJXSQJR-UHFFFAOYSA-N 0.000 description 1
-1 3-nitro2-pyridylmercapto Chemical class 0.000 description 1
OKTJSMMVPCPJKN-UHFFFAOYSA-N Carbon Chemical compound [C] OKTJSMMVPCPJKN-UHFFFAOYSA-N 0.000 description 1
239000007868 Raney catalyst Substances 0.000 description 1
NPXOKRUENSOPAO-UHFFFAOYSA-N Raney nickel Chemical compound [Al].[Ni] NPXOKRUENSOPAO-UHFFFAOYSA-N 0.000 description 1
229910000564 Raney nickel Inorganic materials 0.000 description 1
229960000583 acetic acid Drugs 0.000 description 1
230000002378 acidificating effect Effects 0.000 description 1
125000005233 alkylalcohol group Chemical group 0.000 description 1
230000029936 alkylation Effects 0.000 description 1
238000005804 alkylation reaction Methods 0.000 description 1
230000003110 anti-inflammatory effect Effects 0.000 description 1
DUYAAUVXQSMXQP-UHFFFAOYSA-N ethanethioic S-acid Chemical group CC(S)=O DUYAAUVXQSMXQP-UHFFFAOYSA-N 0.000 description 1
WBJINCZRORDGAQ-UHFFFAOYSA-N ethyl formate Chemical compound CCOC=O WBJINCZRORDGAQ-UHFFFAOYSA-N 0.000 description 1
230000002349 favourable effect Effects 0.000 description 1
239000012362 glacial acetic acid Substances 0.000 description 1
239000002198 insoluble material Substances 0.000 description 1
239000000463 material Substances 0.000 description 1
125000000325 methylidene group Chemical group [H]C([H])=* 0.000 description 1
239000008188 pellet Substances 0.000 description 1
239000002244 precipitate Substances 0.000 description 1
238000002360 preparation method Methods 0.000 description 1
150000003839 salts Chemical class 0.000 description 1
239000002904 solvent Substances 0.000 description 1
239000007858 starting material Substances 0.000 description 1
238000003756 stirring Methods 0.000 description 1

Classifications

- C—CHEMISTRY; METALLURGY
- C07—ORGANIC CHEMISTRY
- C07D—HETEROCYCLIC COMPOUNDS
- C07D513/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00
- C07D513/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having nitrogen and sulfur atoms as the only ring hetero atoms, not provided for in groups C07D463/00, C07D477/00 or C07D499/00 - C07D507/00 in which the condensed system contains two hetero rings
- C07D513/04—Ortho-condensed systems

Definitions

the invention relates to an improved process for preparing 2,3-dihydro-1H-pyrido- [2,3-b] [1,4] thiazines.
Y is bromo, chloro, fluoro or iodo, preferably bromo
R is hydrogen or methyl
R is hydrogen, methyl or ethyl
the Z-mercapto 3 nitropyridine starting material can be prepared according to the method described in J. Pharm. Soc. Japan 64, 201-2 (1944).
the haloacetic acid moieties are commercially available.
the intermediate is then dissolved in 300 m1. of 2- methoxyethanol and hydrogenated in a Parr Shaker in the presence of Raney Nickel at 2 to 3 atm. hydrogen according to the method described in Example 1, lines 20-30 of US. Pat. 3,546,220 to yield 2,3-dihydro-1H- pyrido-[2,3-b][1,4]thiazin-2-one, M.P. 209-211 C.
the alkylation step can be carried out in a number of formamide, dimethylsulfoxide, acetonitrile and C -C alkyl alcohols.
the reaction is generally carried out at temperatures of from 50 to C. for from 1 to 24 hours.
a process for preparing compounds of the formula wherein R and X each represent hydrogen or methyl comprising the steps of reacting a 2-mercapto-3-nitropyridine of the formula ⁇ N/ SH wherein X is hydrogen or methyl, with a haloacetic acid moiety of the formula YCIJHi JORi wherein Y is bromo, chloro, fluoro or iodo, R is hydrogen or methyl and R is hydrogen, methyl or ethyl, in the presence of a suitable solvent to yield a 3-nitropyridin-y1- 2-thioacetic acid moiety of the formula NO; X L

Landscapes

Chemical & Material Sciences (AREA)
Organic Chemistry (AREA)
Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
Pharmaceuticals Containing Other Organic And Inorganic Compounds (AREA)

US00108206A 1971-01-20 1971-01-20 Method of preparing 2,3-dihydro-1h-pyrido-(2,3-b)(1,4)-thiazin-2-ones Expired - Lifetime US3749715A (en)

Applications Claiming Priority (1)

Application Number	Priority Date	Filing Date	Title
US10820671A	1971-01-20	1971-01-20

Publications (1)

Publication Number	Publication Date
US3749715A true US3749715A (en)	1973-07-31

Family

ID=22320864

Family Applications (1)

Application Number	Title	Priority Date	Filing Date
US00108206A Expired - Lifetime US3749715A (en)	1971-01-20	1971-01-20	Method of preparing 2,3-dihydro-1h-pyrido-(2,3-b)(1,4)-thiazin-2-ones

Country Status (9)

Country	Link
US (1)	US3749715A (fr)
BE (1)	BE768305A (fr)
CA (1)	CA932733A (fr)
CH (1)	CH540287A (fr)
DE (1)	DE2109636A1 (fr)
FR (1)	FR2122826A5 (fr)
GB (1)	GB1321360A (fr)
SE (1)	SE372018B (fr)
ZA (1)	ZA711249B (fr)

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20040002495A1 (en) *	2002-05-20	2004-01-01	Philip Sher	Lactam glycogen phosphorylase inhibitors and method of use

1971
- 1971-01-20 US US00108206A patent/US3749715A/en not_active Expired - Lifetime
- 1971-02-26 ZA ZA711249A patent/ZA711249B/xx unknown
- 1971-03-01 DE DE19712109636 patent/DE2109636A1/de active Pending
- 1971-03-01 SE SE7102579A patent/SE372018B/xx unknown
- 1971-03-26 CA CA108828A patent/CA932733A/en not_active Expired
- 1971-04-19 GB GB2567271*A patent/GB1321360A/en not_active Expired
- 1971-06-09 BE BE768305A patent/BE768305A/fr unknown
- 1971-06-09 FR FR7120967A patent/FR2122826A5/fr not_active Expired
- 1971-06-11 CH CH854671A patent/CH540287A/fr not_active IP Right Cessation

Cited By (4)

* Cited by examiner, † Cited by third party
Publication number	Priority date	Publication date	Assignee	Title
US20040002495A1 (en) *	2002-05-20	2004-01-01	Philip Sher	Lactam glycogen phosphorylase inhibitors and method of use
US7057046B2 (en)	2002-05-20	2006-06-06	Bristol-Myers Squibb Company	Lactam glycogen phosphorylase inhibitors and method of use
US20060128687A1 (en) *	2002-05-20	2006-06-15	Philip Sher	Lactam glycogen phosphorylase inhibitors and method of use
US7425550B2 (en)	2002-05-20	2008-09-16	Bristol-Meyers Squibb Company	Lactam glycogen phosphorylase inhibitors and method of use

Also Published As

Publication number	Publication date
GB1321360A (en)	1973-06-27
FR2122826A5 (fr)	1972-09-01
ZA711249B (en)	1971-11-24
DE2109636A1 (de)	1972-08-03
BE768305A (fr)	1971-12-09
CA932733A (en)	1973-08-28
SE372018B (fr)	1974-12-09
CH540287A (fr)	1973-08-15

Publication	Publication Date	Title
US3767667A (en)	1973-10-23	Process for preparing 1h-tetrazole compounds
SU566524A3 (ru)	1977-07-25	Способ получени производных пиридо(1,2-а)-пиримидина или их солей
Boothe et al.	1958	Chemistry of the Tetracycline Antibiotics. 1 I. Quaternary Derivatives
US3749715A (en)	1973-07-31	Method of preparing 2,3-dihydro-1h-pyrido-(2,3-b)(1,4)-thiazin-2-ones
NO164353B (no)	1990-06-18	Analogifremgangsmaate til fremstilling av terapeutisk aktive pyridopyrimidiner.
US3496196A (en)	1970-02-17	4,6-diazido-4,6-dideoxy-myo-inositol tetraacylates
US3176017A (en)	1965-03-30	Aroylalkyl derivatives of diazabicyclo-nonanes and-decanes
US3546220A (en)	1970-12-08	2,3-dihydro-1h-pyrido-(2,3-b)(1,4)thiazines
US3316251A (en)	1967-04-25	5, 6-dihydro-5-oxo-11h-pyrido-[2, 3-b][1, 5]-benzodiazepine derivatives and process
US2943092A (en)	1960-06-28	Method of preparing 4-amino-3-isoxazolidinones
US3036081A (en)	1962-05-22	4, 5-benzo tryptamine and process of producing same
US2637731A (en)	1953-05-05	Imidazopyridines
US3058992A (en)	1962-10-16	Intermediates for the preparation of
US2839529A (en)	1958-06-17	Isothiazole compounds
US3821214A (en)	1974-06-28	Oxazine derivatives
DE2939224A1 (de)	1980-04-17	Imidazo eckige klammer auf 2',1' zu 2,3 eckige klammer zu thiazolo eckige klammer auf 5,4-c eckige klammer zu pyridine
PL149618B1 (en)	1990-03-31	Method of obtaining novel derivatives of pyrimidine
DE3913756A1 (de)	1990-10-25	8(beta)-substituierte ergoline, verfahren zu ihrer herstellung und ihre verwendung
US3177216A (en)	1965-04-06	4-trifluoromethyl-2-thio-5h-alka[d]-pyrimidines and congeners
US3346568A (en)	1967-10-10	2-amino-5-sulfamyl-benzoic acid hydrazides
US2809199A (en)	1957-10-08	Process and intermediates for preparing rauwolscine and derivatives
US2988552A (en)	1961-06-13	Process of preparing 2, 3-seco-3-oxo-20alpha-yohimbane compounds and products obtained thereby
US3423412A (en)	1969-01-21	Benzopyrroloquinazolinones
US3314951A (en)	1967-04-18	Spiro(indoline-3, 2'-[2h-1, 3]thiazin)-2-ones and derivatives thereof
US3268554A (en)	1966-08-23	Substituted endo-perhydro-4, 7-methanoisoindoles and intermediates therein